Oxygen → 2-(3-chloro-phenyl)-2H-tetrazol-5-yl-ethanol

Participants

Reaction Steps

Ozone was bubbled through a solution of 2-(3-chlorophenyl)-5-[1-methyl-2-phenylvinyl]-2H-tetrazole (2.73 g, 9.2 mmol) in methanol (75 mL) and dichloromethane (75 mL) at −78° C. When the color lightened and the starting material had disappeared by TLC, oxygen was bubbled through the mixture for approximately 2-3 minutes. Sodium borohydride (635 mg, 16.8 mmol) was added. The reaction was allowed to warm to room temperature, stirred for 30 minutes and quenched with water (5 mL) and saturated ammonium chloride (5 mL). After removal of the solvent in vacuo, the product was partitioned between dichloromethane and water, dried over sodium sulfate, and the solvent was removed in vacuo. Flash chromatography (15-35% ethyl acetate in hexane) yielded the title compound as a yellow solid (1.795 g, 87%). 1H NMR (CDCl3) δ (ppm): 8.19 (m, 1H), 8.06 (m, 1H), 7.50 (m, 2H), 5.3 (m, 1H), 2.54 (m, 1H), 1.78 (d, 3H).

Provenance & Evidence